反应详情

A solution of 4.0 g of phenylacetyl chloride in 10 ml of chloroform is added dropwise to a stirred solution of 4.0 g of 2,3-dihydrospiro[benzofuran-2,3'-pyrrolidine], free base of Example 8, and 3 ml of triethylamine in 40 ml of chloroform. After total addition, the reaction mixture is stirred successively at ambient temperature for 18 hours and at reflux for 3 hours and then permitted to cool to ambient temperature before being poured into 100 ml of water. The organic layer is collected and then washed sequentially with dilute acid, dilute base, a saturated sodium chloride solution and dried. Thereafter, the solvent is evaporated off, leaving a dark oil which is chromatographed through a silica gel column with a 5% methyl alcohol in chloroform eluant, leaving a light yellow oil. This oil is triturated with boiling hexane, the triturant is decanted and allowed to cool, which causes a precipitate to appear. The precipitate is collected and recrystallized twice from hexane to give the pure product, 2,3-dihydro-1'-(phenylacetyl)spiro[benzofuran-2,3'-pyrrolidine], mp 98°-99° C.

1. additionAfter total addition
2. temperatureat reflux for 3 hours
3. temperatureto cool to ambient temperature
4. customThe organic layer is collected
5. washwashed sequentially
6. additionwith dilute acid
7. additiondilute base
8. dry with materiala saturated sodium chloride solution and dried
9. customThereafter, the solvent is evaporated off
10. customleaving a dark oil which
11. customis chromatographed through a silica gel column with a 5% methyl alcohol in chloroform eluant
12. customleaving a light yellow oil
13. customThis oil is triturated with boiling hexane
14. customthe triturant is decanted
15. temperatureto cool
16. customThe precipitate is collected
17. customrecrystallized twice from hexane